Analysis of Benzaldehyde Interactions with Nucleosides

Benzaldehyde is present in many commonly consumed foods (ex: coffee, cherries, almonds, and apricots). In addition to its low toxicity, benzaldehyde has been reported to demonstrate anticancer activity. Therefore, there’s interest in determining the mechanisms by which this anticancer activity occurs. Due to the reactivity of other aldehydes, it is proposed that benzaldehyde may form DNA adducts. Calf thymus-DNA was treated with benzaldehyde in the presence of arginine. After enzymatic digestion, it was determined by HPLC that benzaldehyde preferentially reacted with 2’-deoxyguanosine (dG) to form adducts. This selective reactivity of benzaldehyde was also confirmed using 1H NMR. Reaction mixtures of benzaldehyde and arginine with dG and 2’-deoxyadenosine (dA) in [D6]DMSO were prepared. Analysis of the benzaldehyde/dG reaction mixture indicated that there was complete loss of the CHO proton of benzaldehyde and the NH-1 proton of dG.